| 1 | Sat 10 Aug 2019 | 0-0 v Ross CountyHeart of Midlothian 0-0 Ross County | Ladbrokes Premiership |
| 2 | Sun 25 Aug 2019 | 1-3 v CelticCeltic 3-1 Heart of Midlothian | Ladbrokes Premiership |
| 3 | Sat 31 Aug 2019 | 2-2 v Hamilton AcademicalHeart of Midlothian 2-2 Hamilton Academical | Ladbrokes Premiership |
| 4 | Sat 28 Sep 2019 | 0-0 v St MirrenSt Mirren 0-0 Heart of Midlothian | Ladbrokes Premiership |
| 5 | Sun 20 Oct 2019 | 1-1 v RangersHeart of Midlothian 1-1 Rangers | Ladbrokes Premiership |
| 6 | Sun 3 Nov 2019 | 0-3 v RangersRangers 3-0 Heart of Midlothian | Betfred Cup Semi Final |
| 7 | Sat 9 Nov 2019 | 5-2 v St MirrenHeart of Midlothian 5-2 St Mirren | Ladbrokes Premiership |
| 8 | Sat 23 Nov 2019 | 0-3 v KilmarnockKilmarnock 3-0 Heart of Midlothian | Ladbrokes Premiership |
| 9 | Sun 1 Dec 2019 | 0-5 v RangersRangers 5-0 Heart of Midlothian | Ladbrokes Premiership |
| 10 | Sat 21 Dec 2019 | 1-2 v Hamilton AcademicalHamilton Academical 2-1 Heart of Midlothian | Ladbrokes Premiership |
| 11 | Thu 26 Dec 2019 | 0-2 v HibernianHeart of Midlothian 0-2 Hibernian | Ladbrokes Premiership |
| 12 | Sat 1 Feb 2020 | 3-3 v St JohnstoneSt Johnstone 3-3 Heart of Midlothian | Ladbrokes Premiership |
| 13 | Wed 5 Feb 2020 | 2-3 v KilmarnockHeart of Midlothian 2-3 Kilmarnock | Ladbrokes Premiership |
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